Vicinal acylamido sulfonates as lime soap dispersants



United States Patent 3 325 412 VICINAL AcYLAMmo sULFoNATEs AS LIME SOAP DISPERSANTS George L. Broussalian, St. Louis, Mo., assignor to Monsanto Company, St. Louis, Mo., a corporation of Delaware No Drawing. Griginal application Aug. 21, 1962, Ser. No. 218,437. Divided and this application May 21, 1965, Ser. No. 457,845

8 Claims. (Cl. 252-117) This invention relates to soap compositions containing novel lime soap dispersants and more particularly, the invention relates to novel soap compositions containing vicinal acylamido sulfonate or vicinal amido sulfates. The present application is a division of my copending United States patent application Ser. No. 218,437, filed Aug. 21, 1962 and now abandoned.

Soap has been and still is one of the most versatile and inexpensive surface active agents. General use of soap in the home, however, for example, for personal washing and bathing as well as for laundering, is often considered undesirable, because soap forms insoluble scum or curds in wash water that contains significant amounts of the so-called hardness ions such as calcium, magnesium and iron. The curds result from the reaction of the fatty acid anion from the soap with the hardness ions, thus yielding a greasy, Water-insoluble film or curd which ordinarily floats on the surface of the Water and sticks to the surfaces of sinks, tubs, clothes, etc., with which it comes into contact and is removable only with difficulty.

The one method that has become most widely accepted for overcoming the most important of these difficulties which result from using soap in hard water (namely, the elimination or the substantial prevention of the formation of sticky scum [usually called lime soap in the trade] on the surface of the water, which scum often causes the socalled bathtub ring etc.) is that which involves the use of a lime soap dispersant. A lime soap detergent is ordinarily a synthetic surface active agent which, when used in conjunction with the soap, literally causes the lime soap curds to remain mostly dispersed through the water, and eliminates most of their stickiness so that the curds that are formed do not stick to the sinks, bathtubs, etc. in such an undesirable fashion as that described above.

Of the thousands of different synthetic organic surface active agents (often termed surfactants) that have been made over the past thirty or more years, only a very few have the right physical and chemical properties to qualify them for use as lime soap dispersants. At the present time, the actual testing of surfactants as lime soap dispersants remains the only known way to determine whether a given surfactant is an acceptable lime soap dispersant, since minor variations in chemical structure of known surfactants often have great, generally unpredictable effects on their over-all activity as lime soap dispersants. Because of the relative rarity of acceptable, efficient lime soap dispersants, manufacturers of soap products including bar soaps, soap chips and flakes, etc. have very few good lime soap dispersants from which to choose for use in their formulations. In addition, those lime soap dispersants that are presently known and utilized are generally fairly expensive. Thus, there is a strong need in the trade for surfactants that can be utilized to advantage as lime soap dispersants and that can also serve as excellent relatively inexpensive general purpose detergents.

It is a primary object of the present invention to provide novel soap compositions that can be used in hard water without excessive formation of lime soap curds in a sticky, undesirable form.

It is still another object of the invention to provide processes for utilizing these novel surface active agents as general purpose surfactants and as lime soap dispersants.

31,325,412 Patented June 13, 1967 ice Other objects of the present invention will become apparent from the following discussion of the compounds, compositions and processes of the present invention. The novel compounds of this invention that can be use-d as general purpose detergents as Well as lime soap dispersants include those vicinal acylamido sulfonates and sulfates having an aliphatic radical containing from 10 to 30 carbon atoms and an acyla-mido group attached to a carbon atom in said aliphatic radical adjacent to a second carbon atom in said aliphatic radical to which the sulfate or sulfonate group is attached, wherein, the acyl moiety of the acylamido group is either an o group or an acyl group having an aliphatic radical containing from 1 to 5 carbon atoms.

The novel compounds of this invention which are particularly useful as general purpose detergents and as lime soap dispersants are the alkali metal vicinal acylamido sulfo compounds (sulfates and sulfonates) that can be represented by either Formula 1 or Formula 2:

wherein R and R are hydrophobic in nature and are selected from the group consisting of hydrogen and organic radicals containing from 1 to 22 carbon atoms, although it is preferred that the organic radicals be aliphatic, alicylic, substituted aliphatic and substituted alicyclic in nature, that at most one of R and R :be hydrogen, that the sum of the total number of carbon atoms in R and R be from 8 to 22, and that R and R preferably be saturated; R is selected from the group consisting of hydrogen and organic radicals containing at most 5 carbon atoms, R preferably being a saturated alkyl group; and X is selected from the group consisting of sulfonic acid, sulfuric acid, alkali metal sulfonate, alkali metal sulfate, ammonium sulfonate, ammonium sulfate, alkaline earth metal sulfonate and alkaline earth metal sulfate radicals. A and B can be hydrogen, halogens, lower aliphatic (and of these preferably lower alkyl) radicals and halogen-substituted lower aliphatic (preferably lower alkyl) radicals.

When R or R, or both R and R in Formulae 1 and 2, above, are organic radicals, they can be branched or unbranched to practically any degree, although it is pre ferred that they be substantially unbranched (straightchain) and contain a (combined) total of from 8 to 24 carbon atoms. Still further preferred are those in this class of compounds wherein the total number of carbon atoms in R plus R is from 12 to 20. Also, compounds having a structure as in Formulae 1 and 2 wherein one of R and R is hydrogen are particularly preferred embodiments of the present invention. R and R can also contain substituents, which do not render them substantially hydrophilic or water-soluble in nature, such as halides (including fluoride, chloride, bromide and iodide, for example), in their aliphatic or alicyclic radicals, without substantially eliminating the benefit that can result from the use of these compounds as detergents and/or lime soap dispersants. R and R in Formulae l and 2 can also contain, monocyclic hydrocarbyl, polycyclic hydrocarbyl and substituted cyclic hydrocarbyl radicals (whether the rings thereof are saturated or not) although it is preferred that they be aliphatic or substituted aliphatic, rather than alicyclic or substituted alicyclic, radicals. It is additionally preferred that R and R be of the type that does not ordinarily react readily with sulfur trioxide at a temperature below about 35 C., such as, for example, saturated hydrocarbyl, and halidesubstituted hydrocarbyl radicals and the like.

It is preferred, however, that R" be either a lower alkyl saturated hydrocarbyl group or a halogen-substituted saturated lower alkyl hydrocarbyl group containing from 1 to carbon atoms, and even more preferably that R" be aliphatic in nature.

Note that when X is a sulfate group (--OSO M) or a sulfonate group (SO M) in the compounds encompassed by Formulae 1 and 2, above, M is usually a cation selected from the group consisting of alkali metal cations, ammonium cations and alkaline earth metal cations; preferably alkali metal cations, and of these, preferably sodium or potassium.

These preferred vicinal acylamido sulfonates and sulfates can be utilized advantageously as general detergent active ingredients, either alone or in combination with practically any material with which they are compatible in aqueous systems and that can be conventionally employed in combination with known anionic surface active agents such as soap and the alkali metal alkylaryl sulfonates; for example, sodium dodecylbenzene sulfonate. The types of materials that can be employed in the formulation of so-called polyphosphate built detergents, liquid heavy-duty detergents, light-duty detergents, flaked and powdered soap compositions (presuming the usual considerations of compatibility are applied) including such materials as other surface active materials, polyphosphate complexing agents and other builders antiredeposition agents, optical brighteners, bleaching agents and the like, which are well known in the detergent art and need not be detailed here. It is interesting to note that the preferred acylamido sulfo (sulfonate and sulfate) compounds of this invention can be utilized to advantage in practically any of the compositions in which the alkylaryl sulfonates, for example, can be utilized. In order to utilize the compounds of this invention as general purpose surfactants, the compounds need merely be dissolved in effective amounts, generally at concentrations of at least about 0.01 weight percent or more in water. In order for optimum results to be obtained when they are used as lime soap dispersants, these vicinal acylamido sulfo compounds should be dissolved in the hard water either prior to the time, or at the same time, at which the soap is dissolved in the water.

The preferred acylamido sulfonates and sulfates of the present invention, however, have physical and chemical properties that make them particularly outstanding as lime soap dispersants. Therefore, their use as lime soap dispersants constitutes a particularly preferred embodiment of the present invention. Generally, for use as a lime soap dispersant, the acylamido sulfonates and sulfates (preferably the sodium salts, but other alkali metal salts such as potassium and lithium salts or even ammonium salts, can be used) can be blended with any conventional soap (for example, one which is intended to be utilized as a personal or laundry bar soap, or ultimately in the form of soap flakes or powder for laundering purposes) prior to the time the soap is formed into the bar, or before it is ground or flaked to yield the final soap composition. Any amount of the preferred acylamido sulfonate, and/or sulfate and especially amounts above about 1 weight percent (based on the amount of soap in the soap composition into which the compounds of this invention are blended) has a beneficial effect on the lime s-oap curd that forms when the soap composition is dissolved in hard water. However, it is generally preferred that, in combination with a soap (i.e., the alkali metal salt of a fatty acid), between about 5 and about 70 weight percent of one of the preferred vicinal acylamido sulfonates or vicinal acylamido sulfates described above be utilized. Actually, because they are generally solid at room temperature, and generally at temperatures through about 50 C., have a soapy feel, and dissolve relatively slowly (after they are initially compressed into a bar shape) when they are allowed to stand in water, these preferred compounds can even be utilized alone as detergents in the form of bars, flakes, chips, granules, etc., if desired.

The following Table 1 illustrates some of the benefits that can result from utilizing these preferred vicinal acylamido sulfate and sulfonate compounds as lime soap dispersants. The lime soap dispersant test is one that involves the measurement of the relative stickiness of lime soap scum or curds. Lime soap curds are those that form at the surface of hard water after a soap has been dissolved therein. Effective lime soap dispersants decrease or minimize the stickiness of the lime soap curds. In the test, which is conducted at a temperature between and C., 250 parts per million hard water (calculated as CaCO having a CazMg ratio of 2:1 is utilized. Five mls. of a 1 weight percent soap solution (or soap-lime soap dispersant blend) are shaken vigorously in a ml. test tube. Then the resulting foam is immediately stirred slowly into 500 mls. of the hard water in a 600 ml. beaker. After all of the foam is quenched and the solution has stood undisturbed for 2 hours, the amount and particle size of scum, or suspected lime soap curd, are observed and rated in comparison with soap alone and a standard soap-lime soap dispersant composition. Soap gives a low rating of 10, while the standard lime soap dispersed composition is rated 3 in a test such as that just described.

TABLE 1.LIME SOAP DISPERSANCY TEST DATA Sample Tested* Rating (1) Soap-control 10 (2) n-Oi4HziOH-CH1S0 Na 3 NH O O C H3 (3) n-CmHzsCHI-CHOSO;N3 3

NH O 0 0 H3 (4) I1-C14HzqCHCHzNHC 0 CH3 1 S O Na (5) n-CuHn-CI-I-CIfiNHO 0 CH 2 O S O Na (G) nO14HnCHCHnSOsNa 3 NH C 0 C Hz- C H:

(7) C Hi5CHCHzSO Na 1 NH O O CH:

(8) CnHg5-CH-CH2OSO3NB 3 NH O O C H:

S OaNa (9) C H11CH( JH C7H15 5 NH O O 0 H3 (10) Product from Example I, below 2 (11) C1 H35CHCH2SO5K 2 NH O 0 0 11 (12) OmH35CH-CH7OSO3K 2 NH O O C3H7 (13) n-O14HmCHOHzNHC 0 06m 3 O S O NH (14) (O14H CHCHzSO3)1Mg 5 NH O O 0 Ha *Lime soap dispersants tested as a 15 weight percent blend of the dispersant with weight percent of soap.

Although the vicinal acylamido sulfonate compounds of the present invention can be manufactured via several different processes, it has been discovered that one of the most advantageous processes involves the hydrolysis and neutralization of a novel intermediate raw material 2-dioxy-1,2,5-oxathiazine compound which is believed to have a structure such as that shown in Formula 3 or Formula 4:

wherein R, R, R", A and B have the same meaning in Formulae 3 and 4 as they do in Formulae 1 and 2, above. Note that the 2-dioxy-1,2,5-oxathiazines that can be utilized to greatest advantage in the practice of the present invention are the 3- and/or 4- and/or 6 (aliphatic, alicyclic, substituted aliphatic and substituted alicyclic) substituted 2-dioXy-1,2,5-oxathiazines (and similarly substituted 2-dioXy-3,4-dihydro-1,2,5-oxathiazines, 2-dioxy-3,4-dihalo-1,2,5-oxathiazines, or 2-dioxy-3- and/ or 4-mono or di lower alkyl-1,2,5-'oxathiazines); wherein the total (combined) number of carbon atoms in the substituents at the 3- and 4-positions is from 8 to 22, and preferably from '12 to 20, and the preferred substituents at the 3- and 4-positions are saturated aliphatic or halogen-substituted saturated aliphatic in nature.

Still further preferred are those 2-dioxy-l,2,5-oxathiazines having this number of carbon atoms at the 3- or 4-position, but which are only mono-substituted in either the 3- or 4-position. In addition, for the desired lime soap dispersants that can be manufactured via these 2- dioxy-l,2,5-oX-athiazine intermediate raw materials, the 6-position should contain either hydrogen or a saturated aliphatic hydrocarbyl or halogen-substituted saturated hydrocarbyl radical containing from 1 to 8, and preferably -from 1 to 5 carbon atoms (i.e., preferably a lower alkyl radical). Thus, the 2-dioxy-1,2,5-oxathiazine intermediate compounds that can be used to greatest advantage in the processes of this invention are those 2-dioXy- 3,4-dihydro-1,2,5-oxathiazine compounds that contain substituents in the 3- and 4-positions selected from the group consisting of hydrogen, aliphatic hydrocarbyl, alicyclic hydrocarbyl, substituted aliphatic hydrocarbyl and substituted alicyclic hydrocarbyl radicals containing a total of from 8 to 24 carbon atoms in said substituents at the 3- and 4-positions; said 2-dioxy-3,4-dihydro-1,2,5- oxathiazine compounds additionally containing in the 6- position a radical selected from the group consisting of hydrogen, aliphatic hydrocarbyl and substituted aliphatic hydrocarbyl radicals, containing at most 8 carbon atoms. Still further preferred are those 2-dioxy-3,4-dihydro-l,2, 5-oxathiazine compounds having substituents in the 3- and 4-positions that are selected from the group consisting of hydrogen, saturated aliphatic hydrocarbyl and saturated halogen-substituted aliphatic hydrocarbyl radicals containing a total of from 12 to 20 carbon atoms in the 3- and 4-positions; at most one of the 3- or 4-positions containing 2 hydrogens; said 2-dioxy-3,4-dihydro- 1,2,5-oxathiazine compound additionally containing at the 6-position a radical selected from the group consisting of hydrogen, saturated aliphatic hydrocarbyl radicals and halogen-substituted aliphatic hydrocarbyl radicals; said radical at the 6-position containing at most 5 carbon atoms. Still further preferred are those 2-dioxy-1,2,5- ,oxathiazine compounds wherein any organic substituent at the 6-, 3- and/or 4-positions are straight-chain substituents and either the 3- or the 4-posi'tion contains 2 hydrogens. Typical, but non-limiting, examples ofsome of the 1,2,5-oxathiazine compounds from which the desired vicinal acylamido sulfonates of this invention can 'be made are 2-dioxy-3,4-dihydro-4-tetradecy1-6-methyl-1, 2,5 oxathiazine; 2-dioxy-3,4-dihydro-3-methyl-4-decyl-6- ethyl-1,2,5-oxathiazine; 2-dioxy-3,4-dihydro 3 ethyl-4- nonyl-6-allyl-1,2,5-oxathiazine; 2-dioxy 3 heXadecyl-6- phenyl 1,2,5-oxathiazine; 2-di'oxy-3,4-dihydro-3,4-diiso- 'butyl-6-B-methoxyethyl 1,2,5 oxathiazine; 2'dioXy-3,4- dihydro-4-dodecyl-1,2,5-oxathiazine; 2 dioxy-3,4-difiuoro-4-perfluoroctyl-6-trifluoromethyl 1,2,5 oxathiazine; 2-dioxy-3,4-dihydro-3-(7,8-dichlorohexadecyl) 6 chloromethyl-1,2,5-oxathiazine; Z-dioxy 3,4 dihydro-4-(poctyl phenyl)-6-methyl 1,2,5 oxathiazine; 2-dioxy-3- carbethoxyl-hexadecyl--fi-bromoethyl 1,2,5 oxathiazine; 2-dioXy-4-decyl-6-propyl-1,2,5-oxathiazine; 2-dioxy- 3,4-dihydro-3-undecyl-6-hexy1-l,2,5-oxathiazine and the like.

The 2-dioXy-1,2,5-oxathiazines described above can be manufactured by reacting, usually in an appropriate solvent and at a temperature between about 30 C. and about 70 C., an organic nitrile containing from 2 to 8 carbon atoms or hydrogen cyanide with either a B-sultone or a carbyl sulfate type compound in accordance with one of the following reactions:

(5) A B A B R-( 3-( J-R+ R CEN RAM-R 0-302 i l SIO: Sultone Nitrlle (i() (6) A B A B R--(|3--(|}R R"CEN R-(,J-('J-R (I) SIOQ I l SIO:

Son-O Carbyl Sulfate Nitrlle h wherein R, R, R, A and B have the same meanings as those assigned for Formulae l and 2 above. Additional details relating to the manufacture of these 2-dioxy-1, 2,5-0Xathiazines can be found in a patent application, Serial No. 218,438 now Patent No. 3,235,549.

In order to convert any of the above-described 2-dioXy- 1,2,5-oXathiazine compounds to the corresponding vicinal acylamido sulfonic acid, one need merely intermix them in any particularly desired or convenient manner with at least about, but preferably considerably more than, one mole of water per mole of inner anhydride compound and warm the resulting mixture to a temperature above about 50 C., and preferably above about 75 C. If it is desired to convert (hydrolyze) only a portion of the -2-dioxy-1,2,5-oxathiazine material, less than this amount of water can be used. Note that some 2-dioxy-1,2,5-oxathiazine compounds can have more than one of the 2-dioxy-1,2,5-oxathiazine rings (such as'that shown in Formulae 3 and 4 above) per molecule. Thus, when more than one Z-dioxy-1,2,5-oxathiazine ring is present per molecule proportionately more Water than one mole per mole of the oxathiazine compound must be utilized in order to hydolyze all of the inner anhydride rings to the appropriate vicinal acylamido sulfonic acid groups. In order to manufacture a vicinal acylamido sulfonate in accordance with the processes outlined above, the vicinal acylamido sulfonic acids can be neutralized with any alkali metal, alkaline earth metal or ammonium base in either water or a nonaqueous solvent depending upon the solubility characteristics of the particular acid and base that are utilized. Practically any alkali metal, alkaline earth metal or ammonium base that is stable either per se or in aqueous solution within the range of from about room temperature to about C. and

under about one atmosphere of pressure can ordinarily be utilized to convert these sulfonic acids to the corresponding sulfonates. Particularly preferred are the alkali metal cation bases such as alkali metal hydroxides, carbonates, silicates, bicarbonates and the like (and of these, sodium and potassium bases are generally preferred because of economic as well as other considerations) and alkaline earth metal cation bases such as calcium hydroxide, calcium carbonate, magnesium hydroxide, magnesium carbonate and the like. Ammonium hydroxide, as well as other alkaline ammonium salts can also often be utilized to advantage in the neutralization of these sulfonic acids. Water-soluble and/ or waterdispersible bases can conveniently be present in the water that is utilized to hydrolyze the inner anhydride compounds (described above) if desired, to thereby effectively hydrolyze the Z-dioxy-1,2,5-oxathiazine ring and neutralize the resulting acid at practically the same time. Sometimes only a small amount of water (or even none in some instances) is necessary when the hydrolysis and neutralization steps are performed simultaneously. For example, when an alkali metal hydroxide such as sodium, potassium or lithium hydroxide, is utilized after it has been dissolved in an organic solvent such as methanol or ethanol, essentially no additional water at all is needed for the hydrolysis of the 2-dioxy-1,2,5-oxathiazine compound and the formation of the corresponding alkali metal vicinal acylamido sulfonate.

It is advantageous that the hydrolysis and neutralization of the Z-dioxy-1,2,5-oxathiazine compounds can be carried out while the oxathiazine is in physical contact with soap. Thus, soap compositions that have excellent over-all detergent properties, and that are additionally valuable because they can form effectively dispersed lime soap curds when they are dissolved in hard water, can be manufactured directly, if desired, in conventional soap equipment such as a crutcher, or in practically any mixing vessel that can be used to formulate soap (i.e., in which molten soap can be handled), such as a conventional amalgamator, a conventional refiner, or even a conventional soap mill. Since the temperature of the soap when it is in a molten state is generally fairly high, essentially all that is usually necessary to perform the-hydrolysis and neutralization of the 2.-dioxy-1,2,5- oxathiazine compound (admixed with the soap) is that both an effective amount of the oxathiazine compound and a sufiicient quantity of the particular base that is to be employed for the neutralization step be well mixed through the soap while the soap is in the molten state. Usually the small amount of moisture that the molten soap contains is enough for the hydrolysis and neutralization of the oxathiazine to be performed without the necessity of adding water to the molten soap-oxathiazine composition or blend, although some water can be added to speed up the rate of hydrolysis and neutralization of the oxathiazine compound if desired. For this particular neutralization technique, the oxathiazine compound (and the base) can be blended with the soap either before or after the soap is made molten, depending upon the particular manipulative procedure desired. It is generally preferred, however, that an alkali metal hydroxide such as potassium or sodium hydroxide be used when the oxathiazine compound is hydrolyzed and neutralized in situ, i.e., in physical contact with the soap.

After the conversion of the oxathiazine compound to the corresponding vicinal acylamido sulfonate via this technique, the soap-sulfonate compositions can generally be handled via conventional techniques and equipment in a manner similar to that in which plain or conventional soap is handled; for example, through the usual plodding, sizing, cooling, stamping and packaging operations. Ordinarily materials that can be employed with soap (such as preservatives, pigments, dyes, perfumes, fillers and chelating agents) can also be employed in soap compositions that additionally contain any one (or more) of the vicinal acylamido sulfo comr39 pounds of the present invention without detracting substantially from the advantages that can result from practicing the invention. In addition, any soapcan be used advantageously in combination with one or more of the vicinal acylamido sulfo compounds of the present invention.

Another process whereby the vicinal acylamido sulfonates of the present invention can be manufactured is via the treatment (generally in a nonaqueous solvent such as carbon tetrachloride, ethyl ether, benzene and the like) of an appropriate vicinal amino sulfonate with an appropriate carboxylic acid anhydride, generally at a temperature above about 30 C., according to the equation:

wherein R, R, R", A and B have the same meaning as in Formulae 1 and 2, above.

The 2-dioxy-1,2,5-oxathiazine compounds that can be converted by hydrolysis and neutralization into the vicinal acylamido sulfonate compounds of this invention have the peculiar ability to apparently become converted to the corresponding vicinal acylamido sulfonic acids upon being heated in the presence of water (but in the absence of base) as described above, but to revert back to the original 2-dioxy-1,2,5-ozathiazine compound when the temperatures of acidic aqueous systems containing the sulfonic acids are lowered to about room temperature, for example, or sometimes to about a degree or more above about 0 C. However, this reversion in neutral or acidic aqueous media does not ordinarily take place if the particular sulfonic acid utilized (hydrolyzed 2-dioxy- 1,2,5-ox-athiazine) has been reacted with one of the above-described bases. The presence of one or more bases in the aqueous media containing one or more of the above-described 2-dioxy-1,2,5-oxathiazine intermediate compounds generally makes it possible to hydrolyze the inner anhydride (oxathiazine) ring at a lower temperature than would otherwise be expected (of the pure intermediate compounds in neutral or acidic aqueous media, for example).

The vicinal acylamido sulfates of the present invention can be manufactured by first sulfating an appropriate vicinal amino alcohol compound, which in turn can be prepared by reducing an appropriate vicinal amino carboxylic acid such as, for example, an a-amino fatty acid containing from 10 to 26, and preferably from 14 to 22 carbon atoms. After sulfation, the resulting vicinal amino sulfuric acid ester can be reacted, for example, with a lower aliphatic carboxylic acid anhydride such as, for example, acetic, haloacetic or propionic anhydride, to yield the desired vicinal acylamido sulfate compound of the present invention.

In the following examples, which are illustrative of some of the preferred embodiments of the present invention, all parts are by weight unless otherwise specified.

EXAMPLE I Into a conventional glass-lined reaction vessel fitted with a fairly eflicient stirrer are dumped 1,000 parts of powdered 2 dioxy 3,4-dihydro-4-n-tetradecyl-6-methyl- 1,2,5-oxathiazine and 10,000 parts of water. The resulting mixture is then warmed to "and subsequently maintained at a temperature of about C. for about 1 hour, during which time a clarification of the mixture is observed. To this hot mixture is then added enough of a 50 weight percent solution of sodium hydroxide to bring the pH of the hot mixture to about 8. Upon subsequently being cooled to about 0 C., a white precipitate settles out of the aqueous mixture. The precipitate is removed by filtration and airdried to yield a product which is an excellent general purpose detergent and lime soap dispersant. It is practically pure sodium 2-acetamido-n-hexadecanel-sulfonate.

EXAMPLE II Two hundred parts of purified 2-dioxy-3,4-dihydro- 3-n-tetradecyl-6-ethyl-l,2,5-oxathiazine are dispersed in 4,000 parts of water in a conventional glass-lined mixing vessel fitted with a reasonably efiicient stirrer and a Water and/or steam jacket for heating and cooling the contents of the vessel. To the resulting slurry are added 50 parts of a 50 weight percent solution of sodium hydroxide. The resulting mixture is then warmed to a temperature of about 50 C. and held at about this temperature until the mixture becomes clear, at which point essentially all of the anhydride material is hydrolyzed and neutralized to the corresponding sodium sulfonate salt. The resulting compound, sodium 1-propionamidon-hexadecane-Z-sulfonate, is then isolated from the water by drying the neutralized clear solution on a conventional stainless steel drum-drier.

Example III, below, is illustrative of how the vicinal acylamido sulfates of the present invention can be manufactured. Note that a procedure similar to that illustrated in Example 111 can be used to prepare any of the vicinal acylamido sulfates of the present invention.

EXAMPLE III Into a mixing vessel such as that described in Example II, above, are blended 230 parts of 2-amino1-tetradecanol (obtained by a conventional reduction of u-aminomyristic acid with sodium in ethanol) and 250 parts of carbon tetrachloride. The resulting mixture is then cooled to C. To the cold mixture are then added 120 parts of chlorosulfonic acid while the temperature of the mixture is maintained below about 0 C. After the addition of the chlorosulfonic acid is completed (in about 1 hour), the temperature of the resulting blend is slowly (over about 20 minutes) raised to room temperature, after which 250 parts of water are added to the blend. The aqueous blend is then neutralized to a pH of 7.6 with a 50% solution of sodium hydroxide. A precipitate, which forms during the neutralization, is filtered and washed several times with Water, and then several times with carbon tetrachloride, and subsequently air dried. The precipitate is found to be sodium Z-amino-l-tetradecylsulfate.

Fifty parts of the precipitate are then intermixed with 100 parts of acetic anhydride. The resulting mixture is then refluxed at atmospheric pressure for 3 hours. After removal of the excess acetic anhydride and acetic acid via a vacuum distillation, the residue from the vacuum distillation is found to be practically pure sodium 2-acetamido-1-tetradecanesulfate.

EXAMPLE IV In a mixing vessel such as that described in Example H, above, are blended 250 parts of 2-dioxy-3,4-dihydro- 3-1branched heXadecyl-6-benzyl-1,2,5-oxathiazine, 3,000 parts of water, and 150 parts of powdered magnesium carbonate. The resulting mixture is then heated to a temperature of 75 C., and maintained at about this temperature until the evolution of carbon dioxide from the mixture ceases. Then the mixture is filtered to remove excess magnesium carbonate. The resulting filtrate is then spraydried in a conventional spray-drying tower from which the desired product, magnesium 2-benzylamidohexadecane-l-sulfonate, is recovered in a dry, powered form.

What is claimed is:

1. A soap composition consisting essentially of, in addition to a detergent soap, from about 1 to 70 weight percent, based upon the weight of said composition, of a vicinal acylamido sulfo compound having a formula selected from the group consisting of wherein R and R are hydrophobic radicals selected from the group consisting of hydrogen, hydrocarbyl and halogen-substituted hydrocarbyl radicals containing from 1 to 22 carbon atoms; R and R having a combined total of from 8 to 22 carbon atoms, and at most one of R and R being hydrogen; R" is selected from the group consisting of hydrogen and alkyl radicals containing at most 5 carbon atoms; A and B are selected from the group con sisting of hydrogen, halogens, lower alkyl radicals and halogen-substituted lower alkyl radicals; and X is selected from the group consisting of alkali metal sulfonate, alkali metal sulfate, alkaline earth metal sulfonate, alkaline earth metal sulfate, ammonium sulfonate and ammonium sulfate radicals.

2. A soap composition in accordance with claim 1 additionally containing from about 5 to about 70* weight percent of an alkali metal salt of a vicinal acylamido sulfonate having a lower alkyl acylamido group and an alkali metal sulfonate group attached, respectively, at adjacent carbon atoms in a hydrophobic organic compound containing from 14 to 24 carbon atoms.

3. A soap composition as in claim 2, wherein said alkali metal salt is a sodium salt.

4. A soap composition in accordance with claim 1 additionally containing from about 5 to about 70 weight percent of an ammonium salt of a vicinal acylamido sulfonate having a lower alkyl acylamido group and an ammonium sulfonate group attached, respectively, at adjacent carbon atoms in a hydrophobic organic compound containing from 14 to 24 carbon atoms.

5. A soap composition in accordance with claim 1 additionally containing from about 5 to about 70 weight percent of an alkaline earth metal salt of a vicinal acylamido sul fonate having a lower alkyl acylamido group and an alkaline earth metal sulfonate group attached, respectively, at adjacent carbon atoms in a hydrophobic organic compound containing from 14 to 24 carbon atoms.

6. A soap composition as in claim 5, wherein said alkaline earth metal salt is magnesium.

7. A composition according to claim 3 wherein said vicinal acylamido sulfonate is the compound of the formula S OaNa 8. A composition according to claim 3 wherein said vicinal acylamido sulfonate is sodium 2-acetamido-nhexadecane-l-sulfonate.

References Cited UNITED STATES PATENTS 1,932,180 10/ 1933 Guenther et al. 260-401 2,216,617 10/1940 Katz 260401 2,367,010 1/1945 Davis et al. 26O40 1 2,821,536 1/1958 Feichtinger et al. 260-401 2,880,219 3/1959 Burnette et al. 3,187,026 6/1965 Klass 260-401 FOREIGN PATENTS 717,903 11/1954 Great Britain.

LEON D. ROSDOL, Primary Examiner.

ALBERT T. MEYERS, SAMUEL H. BLECH,

I. GLUCK, Assistant Examiners. 

